Patent GB-589340-A (GB)
Title: Manufacture of condensation products, being more especially active vermin combating or insecticidal compounds, and formation of liquid and dry insecticides therewith
IPC: C07C205/16
Filed: 1944-03-04
Abstract: A condensation product having insecticidal properties is made by condensing a 1-phenyl or substituted phenyl - 2 - nitroethanol with an aromatic compound of the benzene series.  The condensation is carried out in the presence of the usual condensation agents such as sulphuric acid, aluminium chloride and zinc chloride.  The products are applied in the form of solutions or emulsions or mixed with inert diluents.  In examples: (1) p-chlorobenzaldehyde and nitromethane are treated with sodium methylate in methyl alcohol to give p-chlorophenyl nitro ethanol which is then reacted with chlorobenzene in the presence of sulphuric acid to form 1 : 1-di-(p-chlorophenyl)-2-nitroethane.  By starting with p-tolualdehyde, nitromethane and toluene there is obtained 1 : 1-di-(p-tolyl)-2-nitroethane, and using 3 : 4-dimethyl-benzaldehyde, nitromethene and o-xylene there is obtained 1 : 1-di-(31 : 41-dimethylphenyl)-2-nitroethane.  (2) The 1-phenyl-2-nitroethanol obtained as in example (1) is condensed with chlorobenzene in the presence of sulphuric acid to give 1-phenyl-1-p-chlorophenyl-2-nitroethane.  Other compounds mentioned which may be produced in an analogous manner are 1-p-tolyl-1-phenyl-2-nitroethane, 1-p-tolyl-1-p-chlorophenyl-2-nitroethane, 1-phenyl-1-(31 : 41-dimethylphenyl)2-nitroethane, 1-p-tolyl-1-(31 : 41-dimethylphenyl)-2-nitroethane, 1 : 1-diphenyl-2-nitroethane, 1 : 1-di-(p-bromophenyl)-2-nitroethane, and 1-(21 : 61-dichlorophenyl)-1-(411-chlorophenyl)2-nitroethane; (3) 1 : 1-di-(p-chlorophenyl)-2-nitroethane in chloroform is mixed with bole and evaporated; (4) 1 : 1-di-p-tolyl-2-nitroethane is mixed with magnesia usta and evaporated; (5) 1 : 1-diphenyl-2-nitroethane in ethyl acetate is mixed with bentonite, evaporated and powdered with gelatine and potassium chromate; (6) calcium carbonate and bentonite are saturated with an alcoholic solution of 1 : 1 - di - p - bromophenyl - 2 - nitroethane and the dried powder mixed with casein, sodium carbonate and a wetting agent such as dodecyl alcohol sulphonate; (7) a solution is prepared of 1 : 1 - di - p - tolyl - 2 - nitroethane methyl hexaline, toluene and soft soap; (8) methyl hexaline is added to a toluene solution of 1 - (21 : 61-dichlorophenyl) - 1 - (411-chlorophenyl) - 2-nitroethane and the product added to a quaternary wetting agent; (9) a toluene solution of 1 : 1-di-p-bromophenyl-2-nitroethane is added to methyl hexaline and the solution added to an aqueous solution of stearyl alcohol sulphonate to form an emulsion; (10) a toluene solution of 1 : 1-diphenyl-2-nitroethane and methyl hexaline is mixed with an aqueous solution of sodium alginate.  If desired, glue, casein, or albuminous decomposition products may be used instead of sodium alginate.ALSO:Insecticides comprise a condensation product of a 1-phenyl or substituted phenyl-2-nitroethanol with an aromatic compound of the benzene series.  Compounds mentioned are 1 : 1-di-(p-chlorophenyl)-2-nitroethane, 1 : 1-di-(p-tolyl)-2-nitroethane, 1 : 1-di-(31 : 41 dimethyl phenyl) - 2 - nitroethane, 1 - p - tolyl-1-phenyl-2-nitroethane, 1-p-tolyl-1-p-chlorophenyl-2-nitroethane, 1 - phenyl - 1 - (31-41-dimethylphenyl)-2-nitroethane, 1-p-tolyl-1-(31 : 41-dimethylphenyl)-2-nitroethane, 1 : 1-diphenyl-2-nitroethane, 1 : 1-di-(p-bromo-phenyl)-2-nitroethane, and 1-(21 : 61-dichlorophenyl)-1-(411-chlorophenyl)-2 - nitroethane.  Additional ingredients of the insecticidal compositions which are mentioned include bole, bentonite, calcium carbonate, casein, glue, gelatine, albuminous decomposition products, methylhexaline, and wetting agents such as dodecyl alcohol sulphonate and stearyl alcohol sulphonate.